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[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-methanol → 3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazole-4-carbaldehyde

HRID 1923572
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HRID 1923572 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13][OH:14])=[C:11]([CH3:15])[O:10][N:9]=2)=[N:6][CH:7]=1>C(Cl)Cl.[O-2].[Mn+4].[O-2]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH:13]=[O:14])=[C:11]([CH3:15])[O:10][N:9]=2)=[N:6][CH:7]=1
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참가 물질

4

반응물 1

HCID 66599256[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-methanol

생성물 1

HCID 866472723-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazole-4-carbaldehyde수율 40.6%

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매2회HCID 6344Dichloromethane용매

실험 절차

To a solution of [3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-methanol (2.10 g, 10.1 mmol) in DCM (240 mL) was added manganese(IV) oxide (activated 85%, 20.63 g, 201 mmol) and the reaction mixture was stirred vigorously at room temperature for 3 days. The reaction mixture was filtered through dicalite and then fresh manganese(IV) oxide (activated 85%, 20.63 g, 201 mmol) was added and the reaction mixture stirred vigorously at room temperature for another 4 days. The reaction mixture was filtered through dicalite and evaporated. The combined DCM extracts were then dried over sodium sulfate, filtered and evaporated. Purification by chromatography (silica, 0 to 50% ethyl acetate in heptane) gave the title compound (845 mg, 40%) as a white solid. MS: m/e=207.0 [M+H]+.

후처리

  1. filtrationThe reaction mixture was filtered through dicalite
  2. stirringthe reaction mixture stirred vigorously at room temperature for another 4 days
  3. filtrationThe reaction mixture was filtered through dicalite
  4. customevaporated
  5. dry with materialThe combined DCM extracts were then dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by chromatography (silica, 0 to 50% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-35f4a96a3148429d92fbd1f8cf80be56
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08178522B2

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